DISGRACELAND - Frank Sinatra Pt 2: New Evidence, Secret Favors, and Three Dead Men. This is Frank Sinatra — Connected, Compromised, and Cornered

Episode Date: July 1, 2025

Frank Sinatra was never just a pop star. In this second chapter of his story, Frank isn’t merely brushing shoulders with gangsters—he’s one of them. Backed by new research and newly released secret intelligence files, this episode unpacks how the Voice became a mafia asset. When Sinatra’s son is kidnapped, before he calls the police—he calls notorious gangster Sam Giancana. And what follows is one of the darkest, bloodiest chapters in music and organized crime history. Is Frank Sinatra the most gangster musician of all time? Tell Jake at 617-906-6638, [e-mail], or on socials @disgracelandpod. To see the full list of contributors, see the show notes at ⁠⁠⁠⁠⁠⁠⁠www.disgracelandpod.com⁠⁠⁠⁠⁠⁠⁠. To listen to Disgraceland ad free and get access to a monthly exclusive episode, weekly bonus content and more, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠⁠⁠⁠⁠⁠⁠. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠⁠⁠ Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠ (formerly Twitter)  ⁠⁠⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠TikTok To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoicesSee omnystudio.com/listener for privacy information.

This is exactly right. Double Elvis. When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands. I vowed, I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends.

Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea with me, Chelsea Handler, we have some fantastic guests like Amelia Clark. When like young people come up to me and they want to be an actor or whatever. My first thing is always, can you think of anything else that you can do? Rather be disappointed in. Do that.

David O'Yellowo. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts. Dennis Leary, Gaten Matarazzo from Stranger Things, Tana Monsu, Camilla Morone, Carrie Kenny Silver, and more. Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Sometimes a suspect is found guilty before a verdict is ever read in court. On the Wicked Words podcast, I talk with the writers who dig deep into the cases that changed history,

including Marsha Clark, who went from prosecuting one of the most famous murder cases to writing crime fiction. It doesn't matter that you didn't take part in the murder. If you were at the scene at all, you're guilty of murder. Every week, the real story is revealed. Join us every Monday for new episodes of Wicked Words. Listen to Wicked Words on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Disgrace Land is a production of Double Elvis.

This is a story about the voice, the weasel, about the boot, and guys named Luffy. Momo and Handsome Johnny. This is a story about the mafia and about one musician's position in the mafia. This is not a story you've likely heard before. This is not just a story about a singer who needed the mob's help. It's about a pop star who was expected to deliver for the mob over and over again and in a way that only made mafia members were expected to deliver. This story is based on recent research from a newish book that pulls from a trove of previously

unreleased secret files from Los Angeles Police Intelligence and FBI documents. This is a story, of course, about Frank Sinatra, a story that puts them not just up close and personal with the mafia, but in the mafia, running illegal errands, entering into illegal businesses, and relying on illegal favors, one of which resulted in not one but three murders. And, this being a story about Frank, the voice, Sinatra, means that it's also a story about great music. Unlike that music I played for you at the top of the show.

That wasn't great music. That was a preset loop from my Melotron called Cowboy Gonna Bleed, mk. I played you that loop because I can't afford the rights to Dominique by the singing none. And why would I play you that specific slice of convent cheese, could I afford it? Because that was the number one song in America on December 8, 1963. And that was the day Frank Sinatra's son was kidnapped and a phone call was made that resulted in the torture and death of three men at the hands of a mafia enforcer.

On this episode, new research, secret files, illegal favors, torture, murder, and Frank Sinatra. I'm Jake Brennan, and this is disgrace land. Once upon a time, back during the earlier part of the 20th century, just after prohibition and throughout the 1940s and 50s, The American mafia consolidated its immense power. And your mafia bosses, your Lucky Luciano's, your Vito Genovese types, created empires. These gangsters, the bosses, picture Don Corleone from the godfather.

They gave orders and stayed above the fray. Below them, there were the captains, the guys who ran the crews. guys like Ruggiero Ritchie the Boot Boyardo from New Jersey who wasn't afraid to get his hands dirty. He was said to bury his enemies in his backyard. And then there was Angelo Gip De Carlo who ran the Jersey labor unions and controlled the nightclub business and who was also known to make enemies disappear.

These were more your Tessio, your fat Clemenza types. Below these guys, you had your soldiers, men like Willie Moretti, a New Jersey member of the Genevese family. Moretti once invited a man who owed him money to dinner to work out his debt. The deadbeat, of course, didn't have the money, and Moretti shot the man in the leg in front of a restaurant full of witnesses, and then finished his meal as if nothing had happened. Moretti himself was shot in the face in 1951,

ironically in a Jersey restaurant while eating a bowl of spaghetti. If you want a comparable character from the godfather for Willie Moretti to continue our analogy, look no further than Vito's muscle, Luca Brazzi. Or better yet, Michael's bodyguard, Al Neri. These mafiosi were so-called made members of the Italian mafia in America, which meant they took blood oaths swearing allegiance to their mob families, swearing to live by the code of Omerta, or silence. Made members of the mafia are protected.

As long as they play by the rules, their bosses and their families are there for them. To keep other gangsters out of their territories, to bail them out of jail, to provide for their families when they get sent to jail, and, generally speaking, to help made men sort out whatever problems they might encounter so that they can continue to earn money for their families and for themselves. being made was and still is one of the highest honors a gangster can receive in the mafia and only Italians can be made. But being made doesn't make you a boss or even a captain. Mixed in among the made soldiers were gangsters who never became made men, but who were nevertheless indispensable to their crime families.

Men like Frank Cheech LeVorci from the Genevese family who ran, ran. New Jersey's gambling and numbers operation. And Ben, Bugsie Siegel, who wasn't even Italian, and who literally built Las Vegas for the American Mafia. The godfathers on Made Men of Influence are, of course, Tom Hagan and Mo Green. Lots of mafiosi are not made men. They're simply connected guys,

but that doesn't mean they're not gangsters. They are. And their fortunes rise and fall with the fortunes of their families. And, and this is the point, not only their fortunes, but their lives depend on their own ability to earn money for their bosses. With that, gangsters win and lose at life accordingly. Nobody likes a loser.

Frank Sinatra especially did not like losers. Mafia bosses like losers even less. Frank Sinatra was a winner, a winning bet. The mafia bet big on Frank at the beginning of his career. The mob was in early on Sinatra, grooming him for stardom before anyone would give the poor son of a broken-down boxer and illegal abortionist a chance. When it mattered most, the mafia used violence to clear the way for Frank and to cash in for themselves. There is a popular myth in our culture. Because Frank Sinatra's parents owned a bar in Hoboken, New Jersey, where known members of the

Jersey and New York mob hung out, that Frank made friends with some unsavory characters back in the day, and that this experience rubbed off on young Frank, and that's where Frank got his wannabe tough guy attitude. It's an attitude that many in Hollywood would joke about, an attitude that those who knew Frank best excused because of his immense fame, an attitude that has been reported to be nothing more than that, just an attitude. Frank flew off the handle sometimes. Sure, but that's just Frank. Oh, yeah, Frank's got some tough guy friends,

but hey, the nightclub business is a tough business. What do you expect? The entertainment world was run by the mob. Most entertainers came in contact with gangsters. Frank's okay. Frank fancies himself a tough guy like the tough guys he grew up with, sure, but Frank's just a wannabe. However, the reality was,

Frank Sinatra wasn't just a wannabe. Frank Sinatra, without being an official made man, was not just friends with some tough guys from back in the neighborhood. Frank Sinatra was himself very much a gangster. Frank Sinatra held the woman by the neck up against the wall. He was so angry he didn't realize he had her feet off the floor. His rage was blinding. At this moment, he didn't even remember what he had done.

But all that Jack Daniels, Frank couldn't not get what he wanted. He was Frank the voice, Sinatra. Charlie Lucky Luciano never had a wait And they never said no to Richie the Boot Boy Ardo Why did this half-ass show girl think she could disrespect him? Through the plate glass window, she went And Frank didn't care who saw it Didn't care even if the president of the United States's brother-in-law,

the actor Peter Lawford, husband of Patricia Kennedy, saw it. Peter later went on record with this story about Frank and the working girl and the plate glass window And fuck Peter and fuck his wife too, which Frank figured he would likely do again at some point. Sleeping with the president's sister, only further embedded Frank inside Camelot, which was a relationship Frank Sinatra cared about almost as much as his relationship with the mob, or the boys, as he called them.

Peter Lafford wasn't the only one flapping his gums. Sammy Davis Jr. talked to a Chicago radio station in the 60s and had the nerve to tell a DJ that, quote, I love Frank, but talent is not an excuse for bad manners. I don't care if you are the most talented person in the world. It does not give you the right to step on people and treat them rotten. This is what he does occasionally, end quote. In Chicago, Sammy said this on a Chicago radio station,

in Sam Momo Giancana's town. Frank couldn't have this. Frank was just as indebted to Giancana now in the early 1960s, as he'd been indebted back in 1946 to Giancana's then-bossi. Tony Acardo, the former bodyguard for Al Capone. But back in 1946, Al Capone was dying of syphilis in Miami, just 200 miles away from Cuba, where Capone Chicago was being represented by his cousins, Rocco and Charles Fichetti. At this moment, in 1946, those two gentlemen were on a plane seated next to Frank Sinatra,

who had a bag at his feet that was stuffed with cash in a 32-rorororororo. revolver. All the boys knew the Fichetti cousins, and everyone knew Frank Sinatra, big star that he was back in 46, and that was the genius of using Frank as the bagman. No one was going to search Frank Sinatra upon landing at Rancho Boero's airport that December weekend among a flood of American mob, soldiers, and bosses. Vito Genovese, Frank Costello, Albert and Estacia, Joe Bonano, Santo Traficante Sr., and Carlos Marcello among them. The so-called Havana conference was set up in part to pay tribute to Charlie Luciano, thus the bag of money.

And the Havana conference was set up so Luciano and his partner, Meyer Lansky, could entice other crime bosses to invest in Havana's casinos. Cuban leadership, particularly the former president and military dictator, Fligensio Batista, was beyond corrupt, and they had sold the country out to American. mob interests. Havana was 100% owned by Luciano and Lansky, and now Luciano and Lanski were opening it up for business. That weekend, there would be all manner of entertainment for the U.S. gangsters, showgirls, prostitutes, floor shows, depraved acts of bestiality, whatever they desired,

and of course, a private performance by the biggest star on the planet at the time, their own Frank Sinatra. After his performance, the very much married Frank Sinatra settled into his suite at the Hotel Nacional with his girlfriend for the weekend, Allora Gooding. When Allura awoke after they had sex, she heard a loud banging outside. Out the window, from beyond the terrace, she saw two guards sprinting straight for their room. What were they carrying? Frank, get up! They have guns! They're coming to kill us! Frank sprung out of bed and went for his 32.

The guards were now at the door yelling in Spanish, and Allura grabbed the rifle they had in the room for extra protection, and there was more yelling, and in a language Allura did not understand, Allura pointed the rifle and fired. One guard fell, dead on the spot. Then, another shot. This one from behind the guards, this one from the pistol of a hotel security man sprinting toward the cluster fuck in Frank Sinatra's suite.

A cluster fuck just made worse due to the fact, that the second shot killed the other guard at the door. It all happened before Frank's eyes had time to focus. He turned to his date. You killed that guy. Alora protested. They were coming to kill us. They had guns.

Frank looked down at the bloody mess in the doorway. Those weren't guns? Those were walkie-talkies. The event was not sorted out by local lawmen, attorneys, or judges. Justice was not sought. or served. Frank never called the cops or his lawyer back in New York. Instead, Frank's gangster buddy sent Allure Gooding home quietly to the states, while mafia-controlled Cuban soldiers cleaned up the mess.

Frank Sinatra went about his business that weekend, reveling in the festivities, secure in the fact that the mafia wasn't going to let anything as insignificant as a couple of dead Cubans submarine their investment in Havana, or in their investment in one of their top earners. Him, Frank, the voice, Sinatra. There's two golden rules that any man should live by. Rule one, never mess with a country girl. You play stupid games, you get stupid prizes.

And rule two, never mess with her friends either. We always say that trust your girlfriends. I'm Anna Sinfield, and in this new season of the girlfriends, Oh my God, this is the same man. A group of women discover they've all dated the same prolific con artist. I felt like I got hit by a truck. I thought, how could this happen to me? The cops didn't seem to care.

So they take matters into their own hands. I said, oh, hell no. I vowed. I will be his last target. He's going to get what he deserves. Listen to the girlfriends. Trust me, babe. On the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. This season on Dear Chelsea with me, Chelsea Handler, we have some fantastic guests like Amelia Clark.

When like young people come up to me and they want to be an actor or whatever, and my first thing is always, can you think of anything else that you can do? Rather be disappointed in. Do that. Dennis Leary. I wake up and I'm hitting him in the head with a water bomb. And Bruce Jenner is on the aisle in a karate stance like he's about to attack me. They're like, making karate noises.

And here's the entire the Kardashian family over there. Everybody's going, and the air marshal is trying to grab my arms and screaming. I immediately know that I've been a sleepwalking. David O'Yellowo. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts.

Guy Branham. So anyway, Nicole Kidman broke up with Keith Thurban. Being half of a country couple was always a hat she was going to wear, not like a life she was going to lead. Oh, interesting. I like that. Did you practice that on your way over? Gaten Matarazzo from Stranger Things. Tena Monsu.

Camilla Morone at Carrie Kenny Silver. And more. Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Kate Winkler Dawson, host of the Wicked Words Podcast. Each week I sit down with the true crime writers behind some of the most compelling true crime stories and discuss their years spent investigating and why it still matters. He sees his father coming out of the woods with his hands over his face, and he knows something happened.

His father just grabs him and says she's gone. She's gone. These are the cases that leave survivors, families, and the journalists who cover them changed forever. Working in national television, it'll push you to your limits, and you'll end up doing things you never thought you do. You know, you look back at it and you're like, I can't believe that really happened. Join me and step inside the investigation. New episodes drop every Monday on the exactly right network. Listen to wicked words on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. They say that in the mafia, you're only as good as your next envelope, meaning you're valued.

only by how much money you earn for your boss. Mafia soldiers don't earn salaries. They make their money criminally, and they pay a portion of that money regularly to their bosses as tribute. In return, the boss protects them from other violent mobsters and provides resources to help them commit their crimes. That's the deal. It's that simple.

Frank Sinatra was a special case. He wasn't good with a gun. He wasn't a hitman. Wasn't a safecracker or a second-story man. Wasn't an arsonist, extortionist, or bookmaker. All standard mafia occupations. Frank Sinatra was none of these things. Frank was a song and dance man. But just because Frank Sinatra's talent wasn't inherently criminal, it didn't mean Frank Sinatra didn't make money for the mom. He did. Frank Sinatra didn't just make money for the mob because they were friends he knew from back in the old neighborhood. Guys who may or may not have exploited him to act out of some sense of childhood loyalty or otherwise. No. Frank Sinatra did favors for the mob and he earned for the mob because, for all intents and purposes,

Frank Sinatra was in the mob. I realize how ridiculous this sounds, but hear me out. Mafia soldiers, unmade men, they don't create a resume and sit down for job interviews with prospective mob families to obtain their jobs. Instead, they come up through the ranks in their respective neighborhoods organically. Maybe a connected guy does a favor for a maid guy, and the rising hoodlum pays him back with a favor of his own. And thus a bond is created. Further crimes are committed, and naturally, the rising hood is given more. opportunity until he finds himself in the actual employ of the mob, providing and collecting favors,

and now protection, and in return earning regularly for himself and for his new boss. It's a documented fact that the mafia financed Frank Sinatra's early career. They gave him cash for headshots, new suits, even walking around money. And in exchange for these favors, Frank Sinatra performed for the mafiosi. First, in his parents Hoboken Saloon, where they hung out, and eventually in their nightclubs and on their touring circuits. And it is widely accepted as fact, basically admitted by Sinatra himself,

that in 1942, the mob sent William Moretti to pay a visit to bandleader Tommy Dorsey's home because Dorsey was preventing Frank Sinatra from making money. Dorsey had signed Sinatra to a bad contract, a contract that granted the bandleader the rights to one, third of all Frank's earnings for the rest of his life. William already put a gun to Dorsey's head. And if you believe the dramatization of the story and the godfather said to Dorsey, either your brains or your signature is going to be on that contract. Dorsey, of course,

signed, releasing Frank Sinatra from his contract. As far as severed horseheads in the beds of movie moguls, that's a bigger, blurrier dramatization. But again, as it pertains to Frank Sinatra's gangster Bonafides, the outline of the story is true. But despite such protection, by the late 1940s, Frank's career was in serious jeopardy. Hollywood wanted nothing to do with him. He damaged his voice. He lost his recording contract. His relationship with actress Ava Gardner was a tabloid nightmare and he was suddenly considered a has-been. So once again, Willie Moretti stepped in to protect the mafia's investment. Frank wanted the role of Private Maggio

and the new film in production at Columbia Pictures from here to eternity. Emaretti made sure Columbia studio boss Harry Cohn gave it to him. We cover the specifics of this crime in our part one episode on Frank Sinatra. Needless to say, Frank got his way. The film was a hit.

Sinatra won an Oscar for Best Supporting Actor, and just like that, his career was back in business. Now, did Frank Sinatra pay a week? weekly tribute to the mob like other mafia soldiers? No, there's no evidence of that. But part of the deal when you're in the mafia is answering when your boss's call and going to work when they tell you to. And there's plenty of evidence suggesting that the mafia had Frank Sinatra on speed dial, and that when the boys said jump, Frank asked, to the moon or higher, you tell me. We'll be right back after this word, word, word.

There's two golden rules that any man should live by. Rule one, never mess with a country girl. You play stupid games, you get stupid prizes. And rule two, never mess with her friends either. We always say that, trust your girlfriends. I'm Anna Sinfield, and in this new season of the girlfriends... Oh my God, this is the same man. A group of women discover they've all dated the same prolific con artist.

I felt like I got hit by it. a truck. I thought, how could this happen to me? The cops didn't seem to care. So they take matters into their own hands. I said, oh, hell no. I vowed I will be his last target. He's going to get what he deserves. Listen to the girlfriends.

Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea, with me, Chelsea Handler, we have some fantastic guests like Amelia Clark. When like young people come up to me and they want to be an actor or whatever. And my first thing is always, can you think of anything else that you can do? Rather be disappointed in.

Do that. Dennis Leary. I wake up and I'm hitting him in the head with a water bomb. And Bruce Jenner is on the aisle in a karate stance like he's about to attack me. Like making karate noises. And his entire the Kardashian family over there, everybody's going. And the airman. is trying to grab my arms and screaming.

And I immediately know that I've been at sleepwalking. David O'Yellowo. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts. Guy Branham. So anyway, Nicole Kidman broke up with Keith Thurban. Being half of a country couple was always a hat

she was going to wear, not like a life she was going to lead. Oh, interesting. I like that. Did you practice that on your way over? Gaten Matarazzo from Stranger Things. Zana Mujo. Camilla Marone, Carrie Kenny Silver, and more.

Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Remember when you'd walk into your local video rental place and there were always those two employees behind the counter arguing about movies? Well, that's us.

I'm Millie de Cherico. And I'm Casey O'Brien. And now we're arguing about movies on our podcast, Dear Movies I Love You, from the Exactly Right Network. Can I say something about the Criterion Clause? Go ahead, dude. They're letting too many people in there. Okay, that's another film grape I got two. Sadly, that rental place doesn't exist anymore. It's probably a store that sells running shoes.

Or an ice cream shop with an extra pee and an E at the end. So consider us your slacker movie clerks in podcast form. I would like to establish a timeline of the moment you have. figured out who Channing Tatum was. Every Tuesday, we dig into the movies we can't stop obsessing over, from hidden gems to big screen favorites. New

episodes drop every week on the exactly right network. Listen to Dear Movies I Love You on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Given the volatile political situation in Cuba, the mafia hedged their bets by building a second gambling empire,

this one in Las Vegas, Nevada. They invested millions at a time when that really meant something. Frank Sinatra was asked to use his star power to attract other entertainers and thus gamblers to the mob's new playground in Las Vegas. And Frank did just that. Once Cuba fell to Castro in 1959 and the mafia lost their Havana casinos, Las Vegas became even more important to the mob's interests. Years before, Frank Sinatra had been asked to become a partner in a mob-run establishment. A star are like Frank with an ownership stake in a Vegas hotel and casino guaranteed big bucks for the bosses.

And somehow, despite being in major debt to the IRS in the early 1950s, Frank Sinatra was allowed by the Nevada State Gaming Board to invest in the Sands Hotel and Casino and retain a 7.5% ownership piece. Mob boss, Frank Costello, was the majority owner, and Meyer Lansky, Joe Adonis, and Tony Acardo from Chicago, Sam Giancana's boss at the time, also owned stakes. In October 1953, Sinatra performed at the opening of the sands, and he packed them in. The casino hotel was off the ground and running, and Sinatra was thus earning for the mob.

Big time. The mob called upon Frank again, this time in 1960, and Frank, once again, came running. They wanted Frank to be part of another hotel in casino ownership group. This one was on the California-Nevada state line, an existing but financially failing establishment called the Cal Neva. Frank's celebrity could infuse new life into the joint. Along with Frank, Sam Giancana, who by then was the boss of Chicago and one of the most prominent mafia leaders in the country, owned a massive stake in the hotel. The Cal Neva was a big hit. On opening night, in attendance, were not only Sinatra and Giancana, but only Sinatra, but

also the former United States ambassador to the United Kingdom and one-time mob bootleger Joseph P. Kennedy and his son, the U.S. Senator and presidential candidate John F. Kennedy, along with his date, the most famous woman in the world at the time, Marilyn Monroe. Handsome Johnny Raselli was there, too, of course. As were the FBI surveillance agents assembling what would become over the years the biggest FBI file on any entertainer in history. And that entertainer was, of course, Frank Sinatra. Just take a minute to appreciate this astonishing scene. You have one of the richest men in the world, Joseph P. Kennedy, a former ambassador, who, by the way, was there with a date, not his wife.

At the same party, you have his son, a senator, and a man who at that time had a massive national profile because he was running to become the next president. And he's married, and he's there at the same party with his dad, who's with his mistress. and he, JFK, is there with a date. Even though he's married too. And his date is literally the most recognizable woman on the planet, Maryland fucking Monroe. And, and, and the room is stacked full of known gangsters. Sam Giancana, by that point,

was such a notorious criminal that he wasn't allowed to enter any casino throughout the state of Nevada. The Calneva was built on the state line, and the structure straddled both states. Giancana was forced to stay on the California side only. This was not a secret. The gangsters, the corrupt former ambassador,

the adulterous and brazen senator, the glamorous movie star mistress with Frank Sinatra at the center of it all and the FBI listening and snapping picks. Sinatra's friend, the ruthless killer Sam Giancana, had something else in common with Senator Kennedy. They shared a girlfriend, knowing me with a woman named

Judith Exner. Sam Giancano, wily mafioso that he was, knew that he would one day be able to leverage Exner against JFK, a man Giancano was going to make the President of the United States with the help of Frank Sinatra. Just like the story of the mafia freeing Sinatra from Tommy Dorsey's contract by making the bandleader an offer he couldn't refuse, we've come to accept the fact that Joseph P. Kennedy cheated his son's way into the White House by using Frum's, Frank Sinatra as an intermediary between the Kennedy campaign and the mafia, and the Giancana

fraudulently impacted the vote to help the Kennedys, first in the Democratic primary in West Virginia, and then in the general election in Illinois. We look upon this story now as both a fact and as a cute, sly little historical anecdote. No serious historian disputes it. Yet today, any mention of electoral fraud sends people on both sides of the political. spectrum into online hysterics. But again, we take it as gospel that the Democratic nominee used the mafia to cheat his way into the White House with the help of our man, Frank Sinatra. We accept it because it's demonstrably true, because that's how much power the mafia had back in 1960. John F. Kennedy became president, and Sam Giancana and Frank Sinatra put him in the White House.

Yet the president's brother, who is now the Attorney General, Robert F. Kennedy, the most powerful law enforcement officer in the country, would not stop his crusade to destroy Giancana and the mafia. And RFK wouldn't stop because the FBI's Jay Edgar Hoover played RFK a recorded phone conversation between his brother, the married president, and his girlfriend, who was also Sam Giancana's girlfriend. That conversation was recorded on a phone call that Judith Exner made to JFK from Sam Giancana's house. As far as Bobby Kennedy was concerned, Sam Giancana had to go. It was jail or bust.

And Frank Sinatra, he was out as well. The president was, per his brother's instructions, under no circumstances, allowed to carry on his friendship with Frank Sinatra. Frank Sinatra was too close to Sam Giancanares. Kana. Frank was too, gangster. But Frank wouldn't be denied. Frank couldn't be denied. Frank needed his relationship with the president so that he could remain in place as the conduit between the president and the mafia, and thus remain in good standing with Sam G. and Kana. You're only as good as your next envelope. But again, Bobby Kennedy wasn't having it. Bobby Kennedy increased his pressure on the mob, more surveillance, more subpoenas, more arrests, more deportations of mob bosses.

Sam Giancana wanted to know where the Kennedy kids got their balls. Giancana got them elected, and now they betrayed him? The Kennedys, once elected, were supposed to put the mob back into Havana, not into prison, which is what RFK was coming dangerously close to doing. Sinatra was Giancana's only hope. The mafia had given Frank so much. And now the mafia really needed something from Frank. They needed Sinatra to get the Kennedys to back off.

Frank tried, but Frank was out. So Frank threw a Hail Mary. Frank invited President Kennedy to his Palm Springs home for some much-needed R&R. JFK loved Frank's Palm Springs, Pat. It was private and filled with beautiful women. It's where JFK first slept with Marilyn Monroe. Oh, JFK said yes. He was coming to Frank's. And Frank was going to save the day. He'd talk to Jack. Get Jack to talk to Bobby to back off Sam and the boys.

Frank built new quarters on his property for the Secret Service. Frank had a helipad installed. Frank spared no expense. And then Frank got ghosted by the president at the last minute. Bobby had prevailed. Making matters worse, JFK still went to Palm Springs, but he stayed at Bing Crosby's place. Bing was Frank's rival on the charts, and worse, a Republican. Frank Sinatra was out,

and Sam Giancana was pissed. Frank had no juice. Bobby Kennedy was on a warpath. Sam and the rest of the boys had no choice, and John F. Kennedy was now dead. From Washington government sources say that President Kennedy is dead. 16 days after the mafia conspired with the CIA to murder Frank Sinatra's friend,

the sitting president of the United States, Frank sat in his Palm Springs home, wracked with grief, and fearing that because he'd outlived his usefulness, that the mafia was going to kill him next. That's when the unthinkable happened. Frank's son, Frank Sinatra Jr., was kidnapped. The kidnappers weren't fucking around either. They wanted $250,000 in cash or Little Frank was about to become dead little Frank. Frank knew that in moments of crisis, when you

really need something taken care of the right way, like that mess back in Havana with the dead Cubans, when the chips are fully stacked against you, your first call is your most important call. Sinatra picked up the phone. And before we called, his wife before we called the cops or the FBI. He dialed the number of the one man he believed could help him get his son home safely. Mob boss, Sam Giancana. Sam Giancana had his ways of making men talk. Most of them included Sam, Mad Sam, DeStefano, a sadistic enforcer. But this wannabe Nevada cowboy wouldn't talk. The boys from the Calneva pegged him as someone with info on the kidnappers. Frank Sinatra

Jr., just 19 years old, at that point in time launching his own career as a performer, was booked to perform at Harrah's Lake Tahoe Casino, about 12 miles from the Calneva. But instead, Frank Sinatra

Jr. opened the door to his hotel room and found himself staring down the barrel of a gun in his face. On the fucking ground! Within seconds, Two intruders had Frank Jr. blindfolded and bound. They escorted him out of the hotel at gunpoint. Remarkably, without any other hotel guests noticing,

and whisked him away in their Chevy Impala. In Chicago, Sam Giancana dispatched Jimmy the Weasel Fratiano to get to the bottom of where Frank the voice Sinatra's kid was being held. The Weasel turned up this cowboy, and now Mad Sam DeStefano wanted to know what the cowboy preferred the ice pick or the blowtorch. The cowboy, cowboyed up. The blowtorch it was, and the cowboy screamed in agony.

Back in Palm Springs, Frank Sinatra was understandably getting antsy. It had been nearly 18 hours since Junior had been kidnapped. The local authorities hadn't turned up any leads, and Gene Kana's boys weren't doing much better. The cowboy felt the ice pick pierced his skin above his kneecap, and he screamed in horror. Still, he didn't give anything up. By this time, Frank had decided,

decided to fly out to Reno himself to help in search. Frank needed further assurance that his son was going to be returned safely. Frank hedged his bet. And when Frank landed, he immediately went to the FBI, to their makeshift command center to help the feds in their efforts. Frank felt he couldn't count entirely on Sam Giancana. Mad Sam DiStefano switched from the ice pick to something more convincing. He laid the beaten cowboy down on the table and put his head in the vice.

And while the cowboy urinated all over himself in fear, one of Mad Sam's muscle men swung a sledgehammer at his ankle and sent his foot into an ungodly 45-degree angle. This time, there was no scream. This time, the pain was so brutal the cowboy can only huff out short breaths of air and uncontrolled bursts. Meanwhile, over in Reno, the kidnappers had made contact. They demanded a quarter million in cash.

In Palm Springs, Frank's instincts kicked in. Ever the gangster, Frank called on his bagman experience and brought a bundle of cash with him. On the FBI's recommendation, Frank put $250,000 in a suitcase. Frank was understandably anxious, as was Mad Sam. The cowboy wouldn't talk. The cowboy wouldn't give up the whereabouts of Sam G. and Kana's friend, Frank Sinatra's kid. The cowboy wants to be a fucking cowboy? Time then, for the cattle prod.

Mad Sam had his own portable prod customized for occasions just like this. The voltage was calibrated for maximum pain, but not enough to kill. First, he placed the prod on the cowboy's islands. The cowboy's defiance was impressive. Then, the inner thigh. The cowboy pleaded for Mad Sam to stop. He knew what the next stop on the torture trail was, the genitals. But still, he gave Mad Sam nothing other than pleading in defiance.

So Sam had no choice. The prod hit the cowboy's testicles with 5 millimet amps of current and 2,000 watts, and still, the near-dead motherfucker gave up nothing. When Frank Sinatra hit the location for the drop back in Reno, everything went hooey. The kidnappers got antsy and split with Frank Sinatra Jr. down to L.A. Frank knew Giancana had nothing, and Frank began to suspect that Giancana himself was behind the kidnapping, a warning to Frank to keep his mouth shut about the Kennedy assassination.

Frank had no choice. He needed to call in the big gun. To do so, he first called Peter Lofford. Frank knew he couldn't call Peter's wife Patricia Kennedy directly. He was still persona non-grado with the Kennedys. But he knew he could get his friend Peter Lawford to get a word in with his wife, and he knew that there was a chance that Peter's wife would think of Frank fondly after the time they'd spent together, and thus there was a chance that she would call her brother the Attorney General of the United States, the man who controlled the FBI, Sam Giancana's mortal enemy, Robert F. Kennedy.

That's exactly what happened. And despite whatever animus Bobby had toward Frank, Bobby pledged to use his power to help Frank get his son back. The message came back to Sinatra from RFK through Patricia and then through Peter Lawford, and it was this. I know how Frank feels about me, but please tell him everything is being done and we'll get his boy back as soon as possible. While Giancana's man finished off the cowboy by impaling him with a meat hook through the rectum, and while Giancana's other men tortured and killed two more street tufts that, they incorrectly suspected had information on the whereabouts of Frank Sinatra Jr.

Bobby Kennedy flooded Reno in Los Angeles with more FBI agents. He ordered roadblocks at the borders of the state and random police checkpoints throughout California and Nevada. Bobby put the word out. No one was going home until Frank Sinatra got his son back. While the search continued, Bobby eventually called Frank himself to further assure him. everything would be okay. And he was right. Three dipshits, two of whom were former high school classmates of Frank's daughter Nancy, eventually arrived at a separate drop point, this one in L.A. to pick up the ransom money. This time, the money was delivered by Bobby Kennedy's G-man, not by Frank Sinatra, the bagman. With the money in hand, the kidnappers freed Frank Sinatra

Jr. Within 48 hours, all three kidnappers were arrested. Frank Sinatra did something that a lot of gangsters do when they're cornered, when their mafia families can't help them. He went to the feds for help. When Sam Giancana came up with Buckkus, Frank cooperated with the government. Sure, he didn't rat anyone out, but he did do with some mafiosi would consider unthinkable, something that many, many gangsters have been forced to do or otherwise face unthinkable truths. life in prison, the death penalty.

Two fates almost as bad as losing a child. It's hard to blame, Frank, but then again, you and I aren't gangsters. Justice wasn't doled out by Sam Giancana, but by the U.S. court system. Barry Keenan, the ringleader of the kidnapping caper, got life in prison. He served four and a half years. Joe Amsler, the dumber of Barry's accomplices, caught a 75-year sentence. He served three and a half years. John Irwin, the most cooperative of the three, got 16 years.

Ultimately, he served less than two. But three other men, who had absolutely nothing to do with the kidnapping, were tortured and killed by Sam Momo Giancana on behalf of his friend Frank the Voice Sinatra. No doubt Giancana shook this off as no big deal. It was amongst the Italians. He was helping out a friend, helping out a fellow gangster,

which was, without a doubt, a disgrace. I'm Jake Brennan, and this is Disgraceland. I'd hope you dug this episode. Apple podcast listeners, make sure to have auto downloads turned on so you guys never miss an episode of Disgraceland. This week's question of the week is, is Frank Sinatra the most gangster musician of all time? And if not, I want to know who is. Hit me up.

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